The late antique figure of the female monk has been commented upon within the spheres of socio-history, theology, and literary analysis, but no comprehensive study has focused on the contemporary historical and gendered context. This thesis therefore reexamines female transvestite monk hagiographies, revealing that the female protagonists are portrayed as possessing a holy womanhood regardless of having layers of masculinity applied to them. Three layers of masculinity, namely outward, social, and inward, are identified in the characterizations of the female monks. Each masculine layer is scrutinized separately to explore its purpose in the plot structures and to show plausible motivations for the utilization of transvestite figures in religious literature. The use of an intertextual method reveals gendered intertexts, or literary motifs, in the hagiographies which serve as familiar ideological vehicles carrying the intended inspirational, instructional, and theological messages of the writers. Through the removal of these holy women’s masculine layers, this thesis reveals that outward and social masculinity are superficial and heavily relied upon as a means of concealment, but inward masculinity, considered akin to genuine expressions of self in these literary characters, is essentially non-existent. Hagiographers had no intention of transforming their religious protagonists into anything but determined, holy women who are forced to act drastically to sustain ascetic dreams begun while mothers, wives, daughters, and sisters. Masculinities and intertexts located in these Vitae contextualize praise for a holy womanhood within acceptable gendered language, which seems to support a belief in the spiritual potential of women. In comprehending the intertexts’ function in these legends, this thesis highlights the potential for complex irony to develop around the figure of a female transvestite, which supplies religious tales with intrigue and interest, the ability to instruct or chastise mixed audiences, and the potential to portray the reversal inherent in the human drama of salvation.